Twitter, the company he co-founded, is one of the world’s leading social media platforms with 126 million active daily users while another, Square, is a successful mobile payment company. He has an estimated net worth of $5.3bn.

But not all is well in the house that Jack built.

Despite its exponential growth in its early years since 2006, Twitter is failing to attract new users which is causing investors’ much concern, especially when they compare their investment to Silicon Valley rival Facebook and its 1.6 billion users.

The social media giant reported 321 million monthly active users during the fourth quarter of 2018 – losing nine million from the previous year.

Twitter unconvincingly pointed the finger for their disappointing results on various factors such as compliance with GDPR framework, changes to consumer privacy regulations in Europe and the deletion of millions of abusive accounts.

As co-founder, CEO (twice) and former chairman of the board, Jack Dorsey, has played a major role in both the successes and failures of the company.

Like fellow billionaire Elon Musk, Dorsey never shies away from the public eye; happy to air his views on all manner of subjects. Dorsey, apart from a celebrity CEO remains a mega-influencer in the Valley and a wellness guru and a licensed masseur. As with all charismatic business leaders, the companies’ fortunes can rise and fall on the back of their fluctuating egos.

Despite Dorsey’s major contribution in making Twitter a major tech player, there is dark side to the story which often dovetails with Dorsey’s own personal choices, sparking significant backlashes and negative headlines.

In its early days, Twitter revolutionized communication and enabled online and anonymous micro-blogging.

It grew to become the go-to source for breaking news as well as a platform for creating awareness of social justice issues.

It has evolved into a digital archive of our history playing a prominent role in presidential elections and nationwide protests, where people could update and find out what other people are talking about.

However, Twitter has attracted criticism for its perceived failure to prevent the spread of fake news, to stop automated posts from sharing and re-posting and to do enough to remove posts containing harassment, racism, threats, and/or crude language with sufficient speed and conviction.

Researchers from MIT, analysing tweets from three million users over 10 years, showed people are more inclined to re-tweet false reports than true ones and highlighted the role of automated bots in amplifying true stories.

The platform has also come under fire for censoring tweets and removing trending hashtags. Celebrities, like Ed Sheeran have decided to abandon the platform due to trolling and harassment from other users.

From a product perspective, Twitter is treading water, having failed to add anything exciting and substantial to the service besides a new timeline that inadvertently angered its users.

In an effort to remain valuable and relevant over the past two years, Twitter has been experimenting with new features, redesigned user avatars and reply options for users, working towards facilitating first-time users’ experience with the platform, among other changes.

But the micro-messaging service still needs to deal with two great challenges: finding more convincing ways to eliminate harassment and abusive/dehumanizing speech on its platform and to deal with the spread of fake news.

Given these challenges, Twitter has struggled to find a sustainable revenue model and it is still not making a significant dent in digital advertisement, unlike its Valley counterparts. This is even more worrying as digital ad market is expected to continue growing in the following years.

In addition, being best-known for President Trump’s toxic tweets does not really help the platform build its reputation. Trump has repeatedly used his tweets to attack a number of potential advertisers such as Amazon and Nordstrom, causing their shares to drop and limiting any chances they will associate themselves with Twitter.

Without addressing these imminent issues and establishing Twitter as a global hub for real-time conversations free from hate speech, it might be hard for Dorsey to go after his long-expressed political ambitions.

Despite its strong brand name and its prevalence as a favoured communication tool of celebrities and businesses, Twitter needs to re-visit its content design and innovativeness as well as its platform functionality to increase users’ experience and connecting them in real-time or face the prospect of joining MySpace, Friendster and Bebo on the social network junkyard.